Sodium Hydroxide → HCID 69658884, compound

HRID 2212967Notes

Reaction equation

HRID 2212967 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[N:13](S(C2C=CC(C)=CC=2)(=O)=O)[CH:12]=1)=[O:5])[CH3:2].[OH-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69659014HCID 69659014, compound

Product 1

HCID 69658884HCID 69658884, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[5-Cyano-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-cyclopent-1-enecarboxylic acid ethyl ester (2.0 g, 4.6 mMol) was dissolved in THF (100 mL) and sodium hydroxide (1.8 mL, 10 N, 18 mMol) was added. After refluxing for 4 h, the reaction was filtered through celite and the filtrate was evaporated. The residue was dissolved in brine (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organics were dried with magnesium sulfate and evaporated in vacuo. The material was purified by chromatography on silica using ethyl acetate/hexanes (30–40%) as the eluent to provide the product as a white solid (1.21 g, 94%). 1H NMR (400 MHz, CDCl3) δ 8.59 (1H, bs), 7.93 (1H, s), 7.84 (1H, s), 7.40 (2H, s), 4.12 (2H, q, J=7.2 Hz), 3.01 (2H, m), 2.86 (2H, m), 2.02 (2H, pentet, J=7.5 Hz), 1.16 (3H, t, J=7.3 Hz); MS m/e 303.2 (M+Na).

Workup

  1. temperatureAfter refluxing for 4 h
  2. filtrationthe reaction was filtered through celite
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in brine (20 mL)
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. dry with materialThe combined organics were dried with magnesium sulfate
  7. customevaporated in vacuo
  8. customThe material was purified by chromatography on silica

Sources & evidence

ORD record
ord-aa72dc4fed2e4c89a07bd5cf8e98d3ee
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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